2-amino-9-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 2570
• Molecular Formular: C10H13N5O5
• Molecular Mass: 283.24072
• Monoisotopic Mass: 283.09166854
• SMILES: Nc1nc2c(ncn2[C@@H]2O[C@@H](CO)[C@H](O)[C@H]2O)c(=O)[nH]1
• Canonical SMILES: OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6+,9+/m0/s1
• InChIKey: NYHBQMYGNKIUIF-BZKDHIKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: @guanosine
• Synonyms: Guanosine

Database IDs

• CAS Number: 118-00-3
• PubChem SID: 160966020; 46505099
• PubChem CID: 453549

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.155725
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.7063062
• LogD (pH = 7.4): -2.7068908
• Log P: -2.7062182
• Molar Refractivity: 64.6211 cm^3
• Polarizability: 24.328236 Å^3
• Polar Surface Area: 155.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.06
• LOG S: -1.27
• Solubility (Water): 1.53e+01 g/l

PROPERTIES

Physical Property

• Solubility: 0.7 mg/mL at 18 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Hydrophobicity(logP): -1.90 [SANGSTER (1993)]

DETAILS

DrugBank - DB02857

• Drug Groups: experimental
• Description: Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate). [Wikipedia]
• External Links: Wikipedia